تفاعل #1726702

معادلة التفاعل

3-Chloro-4-phenyl-1,2,5-thiadiazole

lithium bis(trimethylsilyl)amide

hydrochloric acid

→

3-amino-4-phenyl-1,2,5-thiadiazole

المردود 68.0%

المذيبات

THF

THF

ظروف التفاعل

المعالجة

1. 1
   استخلاصextracted three times into ether (total 300 ml)
2. 2
   غسيلThe combined organic phases were washed with saturated aqueous sodium bicarbonate and brine
3. 3
   تجفيفdried over magnesium sulfate
4. 4
   تركيزconcentrated in vacuo
5. 5
   workup.DISSOLUTIONThe residue was dissolved in methanol (50 ml)
6. 6
   درجة الحرارةtriethylamine (0.5 ml) was heated
7. 7
   درجة الحرارةto reflux for 15 hr
8. 8
   تركيزagain concentrated in vacuo

الإجراء التجريبي

3-Chloro-4-phenyl-1,2,5-thiadiazole (3.19 g, 16.2 mmol) in THF (32 ml) at 0° C. was treated dropwise with a solution of lithium bis(trimethylsilyl)amide in THF (17.0 ml, 1.0 M, 17.0 mmol). After 10 min the mixture allowed to warm to ambient temperature for 1.5 hr, treated with 1N hydrochloric acid, and extracted three times into ether (total 300 ml). The combined organic phases were washed with saturated aqueous sodium bicarbonate and brine, and dried over magnesium sulfate and concentrated in vacuo. The residue was dissolved in methanol (50 ml) and triethylamine (0.5 ml) was heated to reflux for 15 hr and again concentrated in vacuo. Flash chromatography on silica gel (ethyl acetate/hexanes) yielded 3-amino-4-phenyl-1,2,5-thiadiazole (1.96 g, 68%) as a colorless solid.

المصدر